Buck, have you tried more fried foods and beer?
I went through the same thing with my kid. He was so bad we were giving doctor-order glycerin suppositories, tons of prune juice, fruits, etc, and still got bad enough we had to take him to Children's Urgent Care. After that and 3 trips to a GI specialist, he was put on Miralax. That made all the difference. I hated the idea of a little kid taking daily medicine.
Yep, watching a little one cry after every poop is horrible. Since we're all sharing, my wife had to get scoped (hehe) last year for similar issues and is now taking Lactulose every day.
Who knew so many people had issues shitting?